Herbicidal compositions and herbicidal processes

ABSTRACT

A known antibiotic, SF-1293 substance and salts thereof have now been found to exhibit high herbicidal effects against a wide variety of herbaceous and woody plants, but they are non-phytotoxic particularly to a useful woody plant, Chamaecyparis obtusa. The herbicidal effects of these SF-1293 substances can be noticeably enhanced by applying in combination with certain known herbicides or compounds having biological activities.

This is a continuation of application Ser. No. 959,838, filed Nov. 13,1978.

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to herbicidal compositions, preparation thereofand processes of controlling unwanted plants using the herbicidalcompositions.

2. Description of the prior art

All of the active substances which have hitherto been used as herbicideare the chemically synthetic compounds, which may sometime give rise toproblems of environmental pollution. From a viewpoint of increasinglysevere legal regulations of environmental pollution, the demand nowincreases to provide those herbicidal substances which can be rapidlydecomposed in the surrounding conditions and cause no environmentalcontamination.

We described and claimed the antibiotic, SF-1293 substance and amicrobiological process for the production thereof (see Japanese Pat.No. 827,768, U.S. Pat. No. 3,832,394 and German Pat. No. 2,236,599). Itis now found that the SF-1293 substance as a herbicide can meet therequirements mentioned above since it is susceptible to metabolism andbreakdown into harmless substances in the course of thematerial-circulation occurring in nature.

The SF-1293 substance (in the free acid form) is the compound of theformula: ##STR1##

As described in the aforesaid U.S. and German Patents, the SF-1293substance is highly active to various fungal diseases of plants,including Pellicularia sasakii (sheath blight on rice) and Piriculariaoryzae (rice blast).

SUMMARY OF THE INVENTION

As a result of our further study of the biological activities andutilities of the SF-1293 substance, we have now found that it exhibits aconsiderably high herbicidal effect when applied at a rate of about tentimes higher than that at which it has been used as fungicide. Thus, ithas been found that the SF-1293 substance, and various salts whereof areherbicidally active to growing annual and perennial weeds as well asvarious bushes and trees, and that upon foliage treatment, they canseverely damage or kill the overground segments of the plants andstrongly inhibit regrowth of the plants from their underground rhizomes.

DETAILED DESCRIPTION OF THE INVENTION

According to a most generic aspect of this invention, therefore, thereis provided a process of severely damaging or killing unwanted plants,which comprises applying to the plants or to the growth medium thereof,a herbicidally effective amount of the SF-1293 substance as defined inhereinafter or a salt thereof.

The SF-1293 substance (the free acid form) and salts thereof(hereinafter collectively referred to merely as "SF-1293 substances")are effective to severely damage or kill unwanted plants both whenapplied directly to the plants ("post-emergence application") and whenapplied to soil or other growth medium where the plants are growing, toprevent the emergence of seedlings of the plants ("pre-emergenceapplication").

The SF-1293 substances for use in this invention are advantageous inthat they may be applied at an optional time in all seasons and thatthey are effective not only as a contact herbicide but also as atranslocated or systemic herbicide. Further, they have favorably theunique feature that they are non-phytotoxic to useful woody plant,Chamaecyparis obtusa (Japan cypress, "hinoki" in Japanese, whichprovides a wood material extensively used in the construction offurnitures and houses) but they are highly toxic to unwanted bushes andweeds growing in the area where the useful woody plants occur naturallyor are cultivated artificially.

In a further aspect, therefore, this invention provides a process ofselectively controlling the growth of weeds and bushes in the area ofChamaecyparis obtusa, which comprises applying to the area the SF-1293substance or a salt thereof in an amount sufficient to inhibit thegrowth of the weeds and bushes.

In recent years, infestation of exotic and naturalized weeds andperennial weeds comes into question, and N-phosphonomethylglycin (whichis usually known as glyphosate) is effectively used to control thegrowth of these weeds. It has been observed that the antibiotic SF-1293substance, which acts similarly to glyphosate, is very superior toglyphosate in respect of the herbicidal properties and weed-controlspectrum. Thus, as compared with the glyphosate, the SF-1293 substanceis effective at a lower concentration, more rapidly develops theherbicidal effect and shows a much wider spectrum of weed control, andfurther it is absolutely non-phytotoxic towards Chamaecyparis obtusa asalready stated. In contrast, glyphosate disadvantageously shows aphytotoxicity to Chamaecyparis obtusa. Besides, glyphosate is much lessactive to broadleaved weeds and perennial weeds such as Rumex japonicusand Cayratia japonica. While, the SF-1293 substance is equivalentlyactive against the weeds irrespective of weed species at the sameapplication rate and completely suppresses regrowth or recovery ofperennial weeds.

Generally, non-crop land, orchard, forestry land and grassland can beinfested with annual and perennial weeds and various bushes. In order tocontrol the growth thereof, either treatment of applying a mixture oftwo or more herbicides at once or treatment of applying different orsame herbicide(s) several times at intervals may be employed. Both ofthese herbicidal procedures, however, are very complicated anddisadvantageous in the cost and labor involved therein. The SF-1293substances are highly active against almost all weeds, bushes and treesexcept for Chamaecyparis obtusa, so that application of the SF-1293substances alone can controll all of the undesired plants, inclusive ofweeds and unwanted trees, as intended. Besides, the SF-1293 substancescan prevent regrowth or recovery of the undesired plants, indicatingthat they are a herbicide of particular great value in practice. Thus,the SF-1293 substances are effectively applied for land preparation inforestry land, control of bottom weeds growing in forestry land ofChamaecyparis obtusa, control of weeds and bushes in grassland, bottomweed-control in orchard and inhibition of weed growth in non-crop land,and further they are suitable for pre-sowing treatment in uncultivatedupland, by utilizing their properties that they will become inactivatedat a relatively high rate in soil. The SF-1293 substances are alsosuitable for "spot" herbicidal treatment in crop area or lawn areainfested with vicious perennial weeds.

The SF-1293 substances used in the process of the invention are usuallyapplied in the form of a composition comprising the SF-1293 substancesas the active ingredient which is mixed with a liquid or solid diluentor carrier. In another aspect, therefore, this invention provides aherbicidal composition comprising as active ingredient at least onemember selected from SF-1293 substance of the structural formula:##STR2## and salts thereof, in admixture with a diluent or carrier.

The composition of the invention may generally comprise the activeingredient in an amount of 0.01% to 50 % by weight of the composition.When applied to the herbicidal treatment, this composition usually maybe diluted with water to a concentration of 0.05% to 5% with regard tothe active ingredient.

The salts of the SF-1293 substance which may be used as the activeingredient according to this invention include an alkali metal salt, analkaline earth metal salt, a divalent-metal salt, an unsubstituted orsubstituted ammonium salt or an acid-addition salt which may generallybe represented by the following formula: ##STR3## wherein M¹ and M²,which may be the same or different, each represents hydrogen atom or acation selected from sodium, potassium, lithium, copper, magnesium,calcium, zinc, nickel and manganese, or an ammonium cation eitherunsubstituted or substituted by one, two, three or four lower alkyl,hydroxy-lower alkyl, particularly hydroxyethyl or lower alkenyl group; Arepresents an inorganic or organic acid selected from hydrochloric,sulfuric, hydrobromic, phosphoric, perchloric, nitric, acetic,propionic, citric, tartaric, monochloroacetic, trichloroacetic andtrifluoroacetic acids; and n is 0, 1/2 or 1, p is the inverse number ofthe valency of M¹, and q is the inverse member of the valency of M².

The composition of this invention may be in the form of aqueoussolution, wettable powder, dusting powder, emulsion, granules or grainscomprising the active ingredient in admixture with a suitable diluent orcarrier.

The solid compositions may be in the form of dusting powders orgranules. Suitable solid diluents include kaolin, clay, bentonite,kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia,Fuller's earth, gypsum, Hewitt's earth, diatomaceous earth andvermiculite.

Solid compositions may also be in the form of dispersible powders orgrains comprising a wetting agent to facilitate the dispersion inliquids of the powder or grains which may contain also fillers andsuspending agents.

Liquid compositions include aqueous solution, dispersions or emulsionswhich may be prepared by dissolving the active ingredient(s) in anorganic solvent optionally containing wetting, dispersing or emulsifyingagent(s) and then adding the mixture to water which may also containwetting, dispersing or emulsifying agent(s). Suitable solvents areacetone, isopropyl alcohol, propylene glycol, diacetone alcohol,benzene, toluene, kerosene, methylnaphthalene and cyclohexanone.

By including suitable additives, for example, additives for improvingthe distribution, adhesive power and resistance to rain on treatedsurfaces, the different compositions can be better adapted for intendedpurposes.

The compositions of the invention can comprise also other herbicides orplant-growth regulators known per se, for example, germinationinhibitors so as to envisage enhancement of the herbicidal effect of theSF-1293 substances and extension of a period during which the substancesremain active.

The compositions of the invention may also be in the form of liquidpreparations for use as sprays which are generally aqueous dispersionsor emulsions containing the active ingredient in the presence of one ormore wetting agent(s), dispersing agent(s), emulsifying agent(s) orsuspending agent(s). These agents can be cationic, anionic, non-anionicor ampholytic agents.

Suitable cationic agents are quaternary ammonium compounds, for example,cetyltrimethylammonium bromide and alkylpyridinium chloride. Suitableanionic agents are soaps, salts of aliphatic monoesters of sulphuricacid (for example sodium lauryl sulphate), and salts of sulphonatedaromatic compounds (for example, sodium dodecylbenzenesulphonate,sodium, calcium or ammonium lignosulphonate, butylnaphthalenesulphonate, and a mixture of sodium diisopropyl- andtriisopropylnaphthalene sulphonates). Suitable non-ionic agents are thecondensation products of ethylene oxide with fatty alcohols such asoleyl alcohol or cetyl alcohol, or with alkyl phenols such asoctylphenol, nonylphenol and octylcresol. Other non-ionic agents are thepartial esters derived from long chain fatty acids and hexitolanhydrides, the condensation products of the said partial esters withethylene oxide, and the lecithins. Suitable ampholytic agents arealkyldimethyl betaine and dodecylaminoethyl glycine. Suitable suspendingagents are hydrophilic colloids (for example, polyvinylpyrrolidone andsodium carboxymethylcellulose), and the vegetable gums (for example, gumacacia and gum tragacanth).

The compositions for use as aqueous dispersions or emulsions aregenerally supplied in the form of a concentrate containing a highproportion of the active ingredient, the concentrate being diluted withwater before use. These concentrates often should be able to withstandstorage for prolonged periods and after such storage be capable ofdilution with water in order to form aqueous preparations which remainhomogeneous for a sufficient time to enable them to be applied byconventional spray equipment.

The SF-1293 substance to be used as the active ingredient can beproduced, as described in the specifications of U.S. Pat. No. 3,832,394and German Pat. No. 2,236,599, by a microbiological process comprisingcultivating a SF-1293 substance-producing strain of Streptomyceshygroscopicus under aerobic conditions to produce and accumulate theSF-1293 substance in the culture broth and recoving the active substancefrom the culture broth. A typical example of the SF-1293substance-producing strain of Streptomyces hygroscopicus is a straindesignated as Streptomyces hygroscopicus SF-1293 which has beendeposited in the American Type Culture Collection under ATCC No. 21705and in Japanese public depository "Fermentation Research Institute"under FERM-P No. 996. The salts of the SF-1293 substance may be preparedby any convenient salt-forming method.

The rate of application of the SF-1293 substances required to controlunwanted plants will depend upon the identity of the plant species andthe particular active compound selected for use as well as the climateconditions. However, in general, an application rate of 25 g. to 3000 g.per 10 ares is used. Our experiments have shown that it is mostefficient for the herbicidal purpose to apply at a rate of about 100 lper 10 ares the liquid composition containing 0.01% to 0.05% by weightof the active ingredient to weeds of less than 10 cm in height or theliquid composition containing 0.05% to 0.2% by weight of the activeingredient to weeds of 10 to 30 cm in height.

As stated hereinbefore, the SF-1293 substances are defective not only asthe contact herbicide but as the translocated or systemic herbicide,thereby achieving the regrowth-inhibitory effect which is most importantfor control of perennial weeds and bushes.

We have made great endeavors to utilize the inherent, advantageousfeatures of the SF-1293 substances to a maximum, and as a consequence wehave discovered that the herbicidal effects of the SF-1293 substancescan be appreciably improved when they are applied in combination withone or more known herbicides or other biologically active substances,and particulary in combination with one or more translocated herbicidesor relatively slow-acting herbicides.

According to a still further aspect of this invention, therefore, thereis provided a herbicidal composition comprising as active ingredient amixture of:

(A) at least one member selected from the SF-1293 substance and saltsthereof, and

(B) at least one member selected from choline salt of maleic hydrazide(hereinafter referred to as CMH); phenoxy herbicides; benzoicherbicides; 2,3,-trichlorophenylacetic acid (hereinafter referred to asTPA) and its salts; [(3,5,6-trichloro-2-pyridyl)-oxy]acetic acid(hereinafter referred to as Dowco-233) and its salts;n-phosphonomethylglycine (usually denoted as glyphosate) and its salts;ethyl carbamoylphosphate (hereinafter referred to as DPX-1108) and itssalts;2-(1-allyloxyamino)-butylidene-5,5-dimethyl-4-methoxycarbonyl-cyclohexane-1,3-dione(referred to as NP-48); 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea(hereinafter denoted as Linuron); 3-amino-1,2,4-triazole (hereinafterreferred to as ATA); cholines; and diethylamines.

The phenoxy herbicides include, for example, 2,4-dichlorophenoxyaceticacid (hereinafter referred to as 2,4-D) and salts, allyl ester and ethylester thereof, 2-methyl-4-chlorophenoxyacetic acid (hereinafter referredto as MCP) and salts, allyl ester and ethyl ester thereof,α-(3,4-dichlorophenoxy) propionic acid (hereinafter referred to as3,4-DP) and its salts, d,l-2-(2-methyl-4-chlorophenoxy) propionic acid(hereinafter denoted as MCPP) and its salt, γ-(2-methyl-4-chlorophenoxy)acetic acid (hereinafter denoted as MCPP) and its salt,d,l-2-(2,4,5-trichlorophenoxy) propionic acid (hereinafter denoted as2,4,5-P) and its salts, andα-[4-(3,5-dichloropyridyl-2-oxy)]phenoxypropionic acid (hereinafterdenoted as SL-501) and its salts.

The benzoic herbicides include, for example, 2,3,6-trichlorobenzoic acid(hereinafter referred to as TBA) and its salts,3,6-dichloro-2-methoxybenzoic acid (hereinafter referred to as Banvel-D)and its salts and 3-amino-2,5-dichlorobenzoic acid (hereinafter referredto as Amiben) and its salts.

The cholines include choline itself and choline salts, examples of whichare salts of choline with an inorganic acid such as hydrochloric acid,phosphoric acid and carbonic acid or an organic acid such as aceticacid, oxalic acid and ascorbic acid.

The diethylamines include diethylamine itself and its salts, examples ofwhich are the salt with an inorganic or organic acid same as mentionedabove for the choline salts.

The salts of the SF-1293 substance which may be used in combination withthe component (B) typically include those of the general formula (1) asdefined hereinbefore.

Our extensive studies on mixtures of the SF-1293 substances with otheragents have revealed the following:

Firstly, the herbicidal activity of the SF-1293 substances may besignificantly enhanced when they are applied in combination with a widevariety of herbicides or synergists. In particular, a combination with atranslocated herbicide or relatively slow-acting herbicide leads tomaximum improvement in the herbicidal effect of the SF-1293 substances.

By way of example, as will be seen from Table 8 given hereinbelow,application of 100 l/10 ares of a solution containing monosodium salt ofthe SF-1293 substance used alone at 0.05% concentration gives about 50%kill to Rumex obtusifolius (one of broad-level weeds) but cannot bringabout suppression of regrowth of this weed, whereas application of 100l/10 ares of a solution containing 2,4-D at 0.1% concentration allowsonly bending of the stem and foliage of Rumex obtusifolius but does notexhibit the effect of killing or suppression of regrowth of this weed.In contrast, the application of 100 l/10 ares of a solution containingin combination SF-1293 monosodium salt at 0.05% concentration and 2,4-Dat 0.1% concentration achieves earlier development and pronouncedenhancement of the herbicidal effect of the SF-1293 monosodium salt,resulting in complete kill of the overground segments but in no regrowthfrom the underground rhizomes of this weed. The same can be observed forZoysia japonica which is one of graminaceous perennial weeds. Thus,application of a solution containing SF-1293 monosodium salt at 0.1%concentration gives about 50% kill to Zoysia japonica but allows theregrowth to take place to an extent comparable to the untreated plot atthe lapse of three months after the treatment. While, application of asolution containing 2,4-D at 0.1% concentration exhibits slight orsubstantially no activity to graminaceous plants. On the other hand, theapplication of a solution containing in combination 0.1% SF-1293monosodium salt and 0.1% 2,4-D achieves complete kill and no regrowthwhatsoever at the lapse of three months after treatment, owing to thesynergistically increased activity of the SF-1293 sodium salt. Thus, thecombined use of the SF-1293 substances and a biologically activesubstance with auxin activity (of which 2,4-D is representative) canlead to salient improvement in the contact and systemic, herbicidalactivities of the SF-1293 substances towards both broad-leaved perennialweeds and graminaceous perennial weeds and bring about extremelyimproved effect of inhibiting the regrowth of the weeds.

Such noticeable improvements have been achieved also when CHM which isknown as one of the anti-auxins is applied in combination with theSF-1293 substances, as illustrated in Examples 9-15. Whilst the use ofCMH alone exhibits a very poor herbicidal activity to weeds at growthstage, the combined use of CMH and the SF-1293 substances leads to acharacteristic advantage that the contact herbicidal effect as well asthe regrowth-inhibitory effect by translocation of the SF-1293substances are improved remarkably. For instance, in Example 9, thecombined use of the SF-1293 substances at 0.05% concentration and CMH at0.3% concentration resulted in enhancement of both the contactherbicidal effect (when evaluation is made 21 days after the herbicidaltreatment) and the regrowth-inhibitory effect (when evaluation is made 4months after the herbicidal treatment), as compared to the case when theSF-1293 substances is used alone at 0.1% concentration. Generally, theuse of the SF-1293 substance and CMH in combination allows the effect ofthe SF-1293 substances to be improved by twice and even by four to fivetimes.

In addition, we have found that other various, biologically activecompounds are effective to improve the activity of the SF-1293substances. Among these, the synergism as discussed above has beenobserved with the compounds listed as the Component (B) as statedhereinbefore, and this will be clear from Table 8.

Secondly, the SF-1293 substances exhibit a wider spectrum of weedcontrol when they are applied in combination with the compounds (B), asshown in Examples 11-15. In order to ensure that the SF-1293 substancescan achieve to the utmost the effect of inhibiting the regrowth ofperennial weeds, it is necessary that they should translocate andmigrate into the underground segments of the weed plant after foliagetreatment but before killing of the foliage occurs. In the herbicidaltreatment of plants such as Calystegia hederacea which are verysusceptible of the contact herbicidal effect of the herbicide appliedthereto, it is difficult to inhibit regrowth of this weed from theunderground rhizomes due to that killing of the foliage takes placebefore the SF-1293 substances commence their translocation and migrationinto the underground rhizomes. Nevertheless, the combined use of theSF-1293 substances and the compounds (B) enhances the translocatedherbicidal activity and thus strongly inhibits even regrowth of suchplants as Calystegia hederacea because the combined use of the compounds(A) and (B) can achieve the migration of the active agents into theunderground rhizomes prior to killing of the foliage. All of thecompounds (B) enable extension of weed-control spectra of the SF-1293substances when they are applied in combination therewith. Inparticular, best results can be obtained by combination of the SF-1293substances with CMH as shown in Examples 11-15.

It is known that CMH may suppress regrowth of perennial weeds when it isapplied in autumn season (see Japanese Patent Preliminary PublicationNo. 55835/76). In practical use, however, CMH has the drawback that itcan be normally applied only in autumn season, and that the overgroundsegments of perennial weeds must be removed out by moving when CMH isapplied in spring or summer season for the herbicidal purpose. Asopposed to CMH used alone, when CMH is applied in admixture with theSF-1293 substances, the latter gradually kill the overground segmentswhile both CMH and the SF-1293 substances translocate into and kill theunderground segments of the perennial weeds by the synergistic effect,resulting in complete suppression of regrowth of these weeds. It hasthus been observed that the combined application of CMH and the SF-1293substances ensures the regrowth-inhibiting ability of CMH to display toa satisfactory extent and enables CMH to be applied effectivelythroughout all seasons, which significantly improves the practicalutility of CMH.

Thirdly, the SF-1293 substances have no phytotoxicity to a useful tree,Chamaecyparis obtuse which dominates 25% of the area of the forestryland in Japan, and CMH is also non-toxic to the same. Accordingly,application of a formulation comprising a mixture of the SF-1293substances and CMH to the area of Chamaecyparis obtusa (Japan cypress)resulted in efficient control of unwanted plants, particularly perennialweeds and bushes which are concurrently growing in said area. Besides,CMH, CPX-1108, cholines and diethylamines are likewise non-toxic to thecypress plant.

The compositions comprising a mixture of the SF-1293 substances and thecompounds (B) can be applied for various herbicidal purposes in manyareas and lands including crop area, forestry land, grassland, orchardand non-crop land, as previously described for the compositionscomprising the SF-1293 substances alone as active ingredient. Further,the compositions may be applied in aquatic areas to control aquaticweeds and algae as well as in aquatic rice plant field after the harvestof the ripened rice plants.

The ratio of the SF-1293 substances (A) to the compounds (B) to beincorporated in the compositions may vary over a wide range dependingupon the nature of the compounds (B) and the envisage use of thecompositions. By way of general guidance, however, this mixing ratio maybe in the range from 1:0.2 to 1:20 by weight. Usually, the weight ratioof the SF-1293 substances to each of the compounds (B) may be as shownin Table 1 below.

The total amount of the SF-1293 substance (A) and the compounds (B) inthe herbicidal compositions of this invention may generally be in arange of 0.05% to 80% by weight of the whole compositions. Upon use, thecomposition may usually be diluted to an active ingredient concentrationof 0.05% to 5% by weight. The amount of the SF-1293 substance appliedusually may then be in a range of 25 g to 1500 g per 10 ares.

The compositions comprising the respective active compounds atconcentrations indicated in Table 1 may be applied generally at a rateof 25 to 250 l, preferably 50 to 150 l per 10 ares.

                  TABLE 1                                                         ______________________________________                                                                    Concentration (%)                                                             in formulation to                                 Active Ingredient                                                                             Mixing Ratio                                                                              be applied                                        ______________________________________                                        SF-1293 substances                                                                            1           0.01-1.0                                          SF-1293 substances:CMH                                                                        1:1.0-20.0  0.01-1.0:0.2-1.0                                  SF-1293 substances:2,4-D                                                                      1:0.3-8.0   0.01-1.0:0.05-0.5                                 SF-1293 substances:MCP                                                                        1:0.3-5.0   0.01-1.0:0.05-0.5                                 SF-1293 substances:3,4-DP                                                                     1:0.5-8.0   0.01-1.0:0.05-0.5                                 SF-1293 substances:MCPP                                                                       1:0.3-5.0   0.01-1.0:0.05-0.5                                 SF-1293 substances:MCPB                                                                       1:0.3-5.0   0.01-1.0:0.05-0.5                                 SF-1293 substances:2,4,5-T                                                                    1:0.3-5.0   0.01-1.0:0.05-0.5                                 SF-1293 substances:SL-501                                                                     1:0.5-10.0  0.01-1.0:0.05-0.5                                 SF-1293 substances:2,3,6-TBA                                                                  1:0.3-5.0   0.01-1.0:0.05-0.5                                 SF-1293 substances:Banvel-D                                                                   1:0.3-5.0   0.01-1.0:0.05-0.5                                 SF-1293 substances:Amiben                                                                     1:0.3-5.0   0.01-1.0:0.05-0.5                                 SF-1293 substances:TPA                                                                        1:0.3-5.0   0.01-1.0:0.05-0.5                                 SF-1293 substances:                                                                           1:0.2-6.0   0.01-1.0:0.02-0.2                                 Dowco-233                                                                     SF-1293 substances:                                                                           1:0.3-5.0   0.01-1.0:0.03-0.5                                 Glyphosate                                                                    SF-1293 substances:DPX-1108                                                                   1:0.5-10.0  0.01-1.0:0.1-0.6                                  SF-1293 substances:NP-48                                                                      1:0.5-10.0  0.01-1.0:0.05-0.5                                 SF-1293 substances:Lynuron                                                                    1:0.5-10.0  0.01-1.0:0.05-0.5                                 SF-1293 substances:ATA                                                                        1:0.3-5.0   0.01-1.0:0.05-0.5                                 SF-1293 substances:Cholines                                                                   1:1.0-2.4*  0.01-1.0:0.01-0.8                                 SF-1293 substances:                                                                           1:1.0-2.4*  0.01-1.0:0.01-0.5                                 Diethylamines                                                                 ______________________________________                                         An asterisk (*) indicates molar ratio.                                   

The amount of the SF-1293 substances to be used to kill perennial weedsand bushes and to inhibit regrowth thereof will be affected also by thesurrounding climatic conditions, for example, temperature and intensityof light. By way of example, however, the purposes envisage can beobtained by applying the SF-1293 substances at a rate of: 25 to 600 gper 10 ares for perennial weeds of 1 m or less in height (e.g. Artemisiaprinceps, Rumex japonicus, Cyperus rotundus etc.); 75 to 750 g/10 aresfor perennial weeds of 1 or more in height (e.g. Sasa nipponica,Miscanthus sinensis etc.) and small bushes (e.g. Rhododendron haempferi,Rubus crataegifolins etc.); and 150 to 1500 g/10 ares for big bushes(e.g. Castanea crenata, Quercus serrata etc.) as well as for control offresh sprouts from big stumps.

The compositions comprising the mixed active compounds (A) and (B) canbe formulated into any conventional form, including aqueous solution,dusting powder, wettable powder, emulsion, granule and grain using anyknown solid or liquid diluent or carrier by any convenient method, asdetailed hereinbefore.

This invention is further illustrated but not limited by the followingExamples in which percentages (%) are all by weight unless otherwisestated. In the Examples mono-substituted salts of SF-1293 substance areessentially in the form of the corresponding phosphate (only M¹ in theabove formula (I) is a cation and M² is a hydrogen atom).

Examples 1-3 illustrate the preparation of the compositions according tothe invention.

EXAMPLE 1

    ______________________________________                                        Aqueous solution                                                              ______________________________________                                        (1a)    SF-1293 substance (free acid)                                                                    30.00%                                                     Octylphenylpolyoxyethanol                                                                        10.00%                                                     Methyl para-hydroxybenzoate                                                                      0.15%                                                      Water              54.85%                                             (1b)    Monosodium salt of SF-1293                                                                       10.00%                                                     substance                                                                     CMH                20.00%                                                     Octylphenylpolyoxyethanol                                                                        15.00%                                                     Methyl para-hydroxybenzoate                                                                      0.15%                                                      Water              54.85%                                             ______________________________________                                    

The ingredients listed in above 1(a) and 1(b), respectively, were mixedtogether to prepare an aqueous solution which may be dilued with waterfor use in the foliage treatment.

EXAMPLE 2

    ______________________________________                                        Wettable powder                                                               ______________________________________                                        (2a)    SF-1293 substance (free acid)                                                                    50.0%                                                      Kieselguhr         45.0%                                                      Monosorbitan alkylester                                                                          5.0%                                                       (as surfactant)                                                       (2b)    Mono (diethanolamine) salt of                                                                    15.0%                                                      SF-1293 substance                                                             2,4-D (Na-salt)    30.0%                                                      Kieselguhr         50.0%                                                      Monosorbitan alkylester                                                                          5.0%                                               ______________________________________                                    

The ingredients listed above in 2(a) and 2(b), respectively, weretogether mixed uniformly in the proportions indicated and ground finelyto prepare wettable powders, which are readily dispersible in water andused as, for example, sprays for foliage treatment.

EXAMPLE 3

    ______________________________________                                        Dusting powder                                                                ______________________________________                                        (3a)    SF-1293 substance (free acid)                                                                       5%                                                      Talc                  95%                                             (3b)    Monoisopropylamine salt of                                                                          5.0%                                                    SF-1293 substance                                                             Dowco-233 (Na salt)   5.0%                                                    Talc                  90.0%                                           ______________________________________                                    

Compositions in the form of dusting powder were prepared by mixing andgrinding uniformly all the ingredients listed in above 3(a) and 3(b),respectively, in the proportions stated. The dusting powder may bedirectly applied for foliage treatment at a rate of 0.4 to 6 kg per 10ares.

Examples 4-8 illustrate the herbicidal properties of the SF-1293substances.

EXAMPLE 4 (Pre-emergence test)

Upland soil was placed in a pot of 10 cm diameter and seeds of Digitariaadscendens (Crabgrass) were sown in the soil at a depth of 1 cm. Aftergently pressing the soil surface, the soil was sprayed evenly withsolutions of SF-1293 substance sodium salt dissolved at differentconcentrations in 5 cc of water. 10 Days after spraying, the number ofthe seedlings of crabgrass was counted and percentage (%) of preventionof emergence was evaluated by comparison with untreated plots. Forcomparison, the tests were also conducted using glyphosate instead ofthe SF-1293 sodium salt. The results are shown in Table 2 below.

                  TABLE 2                                                         ______________________________________                                                      Prevention (%) of Emergence                                                   Rate of Application g/10a                                       Test Compounds  0       100     250  500                                      ______________________________________                                        SF-1293 substance                                                                             0       95      100  100                                      (Na salt)                                                                     Glyphosate (isopropyl-                                                                        0        0       0    0                                       amine salt) (Control)                                                         ______________________________________                                    

EXAMPLE 5 (Post-emergence test)

Upland soil was placed in a pot of 10 cm diameter and seeds of crabgrasswere sown in the soil at a depth of 1 cm from the soil surface. When theseedlings grew to a height of about 10 cm, 1.2 ml (equivalent to 100l/10a) of aqueous solutions of the test compounds at differentconcentrations as indicated in Table 3 below were applied evenly forfoliage treatment. 10 Days after treatment, damage to plants wasvisually assessed on a scale of 0 to 10 where 0 indicates no effect and10 indicates complete kill.

The detail of this assessment made in this Example was as follows:

    ______________________________________                                        Scale       Foliage Damage (%)                                                ______________________________________                                        0            0%                                                               1           10%                                                               2           20%                                                               3           30%                                                               4           40%                                                               5           50%                                                               6           60%                                                               7           70%                                                               8           80%                                                               9           90%                                                               10          100%                                                              ______________________________________                                    

The test results are tabulated in Table 3.

                  TABLE 3                                                         ______________________________________                                                     Damage Scale                                                                  Concentration (ppm)                                              Test Compound  0        0.01     0.03 0.1                                     ______________________________________                                        SF-1293 substance                                                                            0        1        8    10                                      (Na salt)                                                                     SF-1293 substance                                                                            0        3        10   10                                      (dimethylamine salt)                                                          Glyphosate (isopropyl-                                                                       0        0        5    10                                      amine salt) (Control)                                                         ______________________________________                                    

The above Table shows that an improved herbicidal effect is exhibited byan organic amine salt of SF-1293 substance.

EXAMPLE 6

Aqueous solutions containing sodium salt of SF-1293 substance atdifferent concentrations as indicated in Table 4 below and 0.1% ofactylphenylpolyoxyethanol as surfactant were prepared and applied at arate of 150 l per 10 ares directly to spontaneously occurring perennialweeds at growth stages indicated in Table 4. 7 Days and 14 days afterfoliage treatment, damage to the plants was vissually assessed on ascale of 0 to 5 where 0 signifies no effect and 5 signifies completekill.

The detail of this assessment made in this Example was as follows:

    ______________________________________                                        Scale       Foliage Damage (%)                                                ______________________________________                                        0           0                                                                 1           20%                                                               2           40%                                                               3           60%                                                               4           80%                                                               5           100%                                                              ______________________________________                                    

One month after treatment, evaluation was made for inhibition ofregrowth expressed in terms of symbols ranging from (-) to (+++) where(-) means no regrowth, namely complete suppression of regrowth, (±)remarkable suppression of regrowth; (+) considerable suppression ofregrowth; (++) medium suppression of regrowth; and (+++) no suppressionof regrowth.

The results are set forth in Table 4.

In the Tables given hereinafter, "SF-1293" means monosodium salt ofSF-1293 substance.

                                      TABLE 4                                     __________________________________________________________________________                                     Scale of Regrowth                                     Damage Scale            Suppression                                           7 Days      14 Days     1 Month                                                     Glyphosate  Glyphosate  Glyphosate                                 Growth                                                                             SF-1293                                                                             (isopropyl-                                                                         SF-1293                                                                             (isopropyl-                                                                         SF-1293                                                                             (isopropyl-                            Test                                                                              Stage                                                                              (Na salt)                                                                           amine salt)                                                                         (Na salt)                                                                           amine salt)                                                                         (Na salt)                                                                           amine salt)                            Plants                                                                            (cm) 0.1%                                                                              0.2                                                                             0.1                                                                             0.2 0.1                                                                             0.2 0.1                                                                             0.2 0.1                                                                             0.2 0.1                                                                             0.2                                  __________________________________________________________________________    Pc  100  4   5 1 2   4 5   2 3.5 - -   + ±                                 Ht  70   4.5 5 3 4   5 5   4 5   - -   - -                                    Ap  50   5   5 3 4.5 5 5   3 4.5 - -   - -                                    Cy  30   4   5 1 2   5 5   1 2   - -   + +                                    Ro  30   4   5 1 2   5 5   2 3   - -   + +                                    Ic  80   4   5 1 1.5 5 5   1.5                                                                             3   - -   + -                                    Pr  5 m  4   5 2 3   5 5   3 4   - -   - -                                    Ms  120  4   5 0.5                                                                             1   4 5   2 3.5 - -   + -                                    __________________________________________________________________________

The names of the test plants are assigned as follows:

Pc: Pleioblastus chino

Ht: Helianthus tuberosus

Ap: Artemisia princeps

Cy: Cayratia japonica

Ro: Rumex obtusifolius

Ic: Imperata cyrindrica

Pr: Pueraria lobata

Ms: Miscanthus sinensis

As seen from Table 4, application of 150 l/10a of a solution containingSF-1293 substance at a concentration of 0.1-0.2% to spontaneousperennial weeds at the growing stage achieved complete kill thereofirrespective of weed species as well as complete suppression ofregrowth.

EXAMPLE 7

Aqueous solutions containing sodium salt of SF-1293 substance atdifferent concentrations indicated in Table 5 below and 0.1% ofoctylphenylpolyoxyethanol as surfactant were applied at a rate of 150l/10a to the area where various bushes were spontaneously growing. Onemonth after foliage treatment, damage to plants was visually assessed ona scale of 0 to 5 where 0 signifies no effect and 5 signifies completekill as described in Example 6.

The results are set out in Table 5.

                  TABLE 5                                                         ______________________________________                                                   Damage Scale                                                                        Overall                                                      Test    Concen-  Evalua-                                                      Compounds                                                                             tration  tion     Sc  Ct   Rb  Zp   Pa  Vb                            ______________________________________                                        SF-1293  0.1%    4        4   4    5   4    4   4                             (Na salt)                                                                     SF-1293 0.2      5        5   5    5   5    5   5                             (Na salt)                                                                     SF-1293 0.3      5        5   5    5   5    5   5                             (Na salt)                                                                     Glyphosate                                                                            0.1      2        1.5 0.5  1   0    3   2                             (isopropyl-                                                                   amine salt)                                                                   Glyphosate                                                                            0.2      3        4   0.5  1.5 1    4   3                             (isopropyl-                                                                   amine salt)                                                                   (Glyphosate                                                                           0.3      4        4.5 1.5  2   2    4.5 3.5                           (isopropyl-                                                                   amine salt)                                                                   Untreated        0        0   0    0   0    0   0                             ______________________________________                                    

The names of the plant species are assigned as follows:

Sc: Smilax china

Ct: Castanea crenata

Rb: Rubus palmatus

Zp: Zanthoxylum piperitum

Pa: Pteridium aquilinum

Vb: Viburnum dilatatum

Table 5 shows that SF-1293 substance also exhibits a high herbicidalactivity against woody plants irrespective of plant species.

Example 8

Aqueous solutions containing sodium salt of SF-1293 substance atdifferent concentrations indicated in Table 6 below and 0.1% ofoctylphenylpolyoxyethanol as surfactant were applied at a rate of 150l/10a to woody plants of about 60-70 cm in height. 7 Days and 14 daysafter treatment, damage to test plants was visually assessed on the samescale (0 to 5) as stated in Example 7. The results are tabulated inTable 6.

                  TABLE 6                                                         ______________________________________                                                   Damage Scale                                                       Test    Concen-  7 Days        14 Days                                        Compounds                                                                             tration  Pd    La  Ch  Cp  Ct  Pd  La  Ch  Cp  Ct                     ______________________________________                                        SF-1293 0.125%   3.5   4.5 0   0   5   5   5   0   0   5                      (Na salt)                                                                     SF-1293 0.25%    4     4.5 0   0.5 5   5   5   0   1   5                      (Na salt)                                                                     SF-1293 0.5%     4     4.5 0   0.5 5   5   5   0   2   5                      (Na salt)                                                                     Glyphosate                                                                            0.125%   0     1   0   0   2   2   2   1   1   3                      (isopropyl-                                                                   amine salt)                                                                   Glyphosate                                                                            0.25%    1     1   0   1   2   3   3   3   3   4                      (isopropyl-                                                                   amine salt)                                                                   Glyphosate                                                                            0.5%     2     2   1   2   3   4   4   4   5   5                      (isopropyl-                                                                   amine salt)                                                                   Untreated        0     0   0   0   0   0   0   0   0   0                      ______________________________________                                    

The names of the test plants are assigned as follows:

Pd: Picea densiflora

La: Larix leptolepis

Ch: Chamaecyparis obtusa

Cp: Cryptomeria japonica

Ct: Castanea crenata

As is observed from Table 6, SF-1293 substance is non-phytotoxic towardsChamaecyparis obtusa even upon the application of 150 l/10a of asolution containing the SF-1293 at a concentration of 0.5%, and thus itcan be used to selectively control weeds and bushes in the forestry areaof the useful plant.

Examples 9-15 illustrates the synergistic effects achieved by thecombined use of the SF-1293 substances (A) and the active compounds (B)as well as the herbicidal effects of the SF-1293 substances used alone.

EXAMPLE 9

Formulations in the form of aqueous solution were prepared comprising asactive ingredient different salts of SF-1293 substance (0.05% or 0.1%)or CMH(0.3%) or mixtures thereof and 0.1% of octylphenylpolyoxyethanolas surfactant. The aqueous solutions were applied at a rate of 100 l per10 ares to Rumex obtusifolius at certain growth stage which wastransplanted into pots of 20 cm in diameter. 21 Days after foliagetreatment, damage to the test plant was visually assessed on a scale of0 to 5 where 0 is no effect and 5 is complete kill as described inExample 6. 4 Months after treatment, further assessment was made bothfor damage to the plant and for suppression of regrowth from theunderground rhizomes which is expressed in terms of symbols ranging from(-) to (+++) where (-) means complete suppression of regrowth and (+++)means maximum regrowth observed as described in Example 6.

The test results are shown in Table 7 below.

                  TABLE 7                                                         ______________________________________                                                     Scales                                                                        21 Days    4 Months                                                           Concentration of SF-1293                                                      substance salt                                                   Test Compounds 0.05%   0.1%   0.05%   0.1%                                    ______________________________________                                        SF-1293 mono-Na salt                                                                         2.5     3.5    0   +++   2.5 ++                                SF-1293 di-Na salt                                                                           2.5     3.5    0   +++   2.5 ++                                SF-1293 mono-K salt                                                                          2.5     3.5    0   +++   2.5 ++                                SF-1293 di-K salt                                                                            2.5     3.5    0   +++   2.5 ++                                SF-1293 mono(isopropyl-                                                                      3       4      0   +++   3   +                                 amine) salt                                                                   SF-1293 mono(n-                                                                              3       4      0   +++   3   +                                 butylamine) salt                                                              CMH (0.3%)     1              0   +++   0                                     SF-1293 mono-Na salt +                                                                       4       4.5    4.5 ±  5   -                                 CMH (0.3%)                                                                    SF-1293 di-Na salt +                                                                         4       4.5    4.5 ±  5   -                                 CMH (0.3%)                                                                    SF-1293 mono-K salt +                                                                        4       4.5    4.5 ±  5   -                                 CMH (0.3%)                                                                    SF-1293 di-K salt +                                                                          4       4.5    4.5 ±  5   -                                 CMH (0.3%)                                                                    SF-1293 mono(isopropyl-                                                                      4.5     5      5   -     5   -                                 amine) salt + CMH (0.3%)                                                      SF-1293 mono(n-butyl-                                                                        4.5     5      5   -     5   -                                 amine) salt + CMH (0.3%)                                                      Untreated      0              0   +++                                         ______________________________________                                    

As is seen from Table 7, the SF-1293 substances used alone at aconcentration of 0.05% to 0.1% cannot achieve satisfactory suppressionof regrowth and CMH used alone exhibits neither herbicidal effect norregrowth-inhibirory effect. However, the combined use of the SF-1293substance and CMH brings about a pronounced synergistic effect, therebykilling the overground and underground segments of the plant, withinhibiting regrowth from the underground rhizomes.

EXAMPLE 10

Aqueous solution containing the SF-1293 substances (A) and thecomponents (B), in admixture or separately, at different concentrationsindicated in Table 8 below were applied at a rate of 100 l per 10 aresto Rumex obtusifolius (abbreviated as Ro) and one of graminaceousperennial weeds, Zoysia japonica (abbreviated as Zy) which had beentransplanted into pots at certain growth stage and taken root firmly inthe pots. 21 Days after foliage treatment, damage to plants was visuallyassessed on a scale of 0 to 5 where 0 is no effect and 5 is completekill as described in Example 6. 3 Months later, further assessment wasmade for suppression of regrowth based on the degree of killing theunderground segments which is expressed in terms of the same symbols asstated in Example 9.

The results are set forth in Table 8, where monosodium salt of SF-1293substance is abbreviated as "SF".

                  TABLE 8                                                         ______________________________________                                                           Scales                                                                        21                                                                            Days  3 Months                                                                later later                                                Test Compounds (Concentration in %)                                                                Ro    Zy    Ro    Zy                                     ______________________________________                                        SF (0.05%)           2.5   1.5   +++   +++                                    SF (0.1%)            3.5   2.5   +++   +++                                    CMH (0.3%)           0     0     +++   ++*                                    CMH (0.6%)           0     0     +++   +*                                     CMH (0.3%) + SF (0.05%)                                                                            4.5   3.5   -     -                                      CMH (0.3%) + SF (0.1%)                                                                             4.5   4     -     -                                      CMH (0.6%) + SF (0.05%)                                                                            5     5     -     -                                      CMH (0.6%) + SF (0.1%)                                                                             5     5     -     -                                      2,4-D (Na salt) (0.1%)                                                                             1     0     +++   +++                                    2,4-D (Na salt) (0.2%)                                                                             2     0     +++   ++*                                    2,4-D (Na salt) (0.1%) + SF (0.05%)                                                                5     3.5   -     +                                      2,4-D (Na salt) (0.1%) + SF (0.1%)                                                                 5     4     -     -                                      2,4-D (Na salt) (0.2%) + SF (0.05%)                                                                5     4.5   -     -                                      2,4-D (Na salt) (0.2%) + SF (0.1%)                                                                 5     5     -     -                                      MCP (Na salt) (0.1%) 1     0     +++   +++                                    MCP (Na salt) (0.2%) 2     0     +++   +++                                    MCP (Na salt) (0.1%) + SF (0.05%)                                                                  4.5   3     +     +                                      MCP (Na salt) (0.1%) + SF (0.1%)                                                                   4.5   4     ±  ±                                   MCP (Na salt) (0.2%) + SF (0.05%)                                                                  5     5     -     -                                      MCP (Na salt) (0.2%) + SF (0.1%)                                                                   5     5     -     -                                      3,4-DP (Na salt) (0.1%)                                                                            1     0     +++   +++                                    3,4-DP (Na salt) (0.2%)                                                                            2     0     +++   +++                                    3,4-DP (Na salt) (0.1%) + SF (0.05%)                                                               4     3     +     +                                      3,4-DP (Na salt) (0.1%) + SF (0.1%)                                                                4     4.5   ±  ±                                   3,4-DP (Na salt) (0.2%) + SF (0.05%)                                                               5     5     -     -                                      3,4-DP (Na salt) (0.2%) + SF (0.1%)                                                                5     5     -     -                                      MCPP (Na salt) (0.1%)                                                                              1     0     +++   +++                                    MCPP (Na salt) (0.2%)                                                                              2     0     +++   +++                                    MCPP (Na salt) (0.1%) + SF (0.05%)                                                                 4.5   3     +     +                                      MCPP (Na salt) (0.1%) + SF (0.1%)                                                                  4.5   4     ±  ±                                   MCPP (Na salt) (0.2%) + SF (0.05%)                                                                 5     5     -     -                                      MCPP (Na salt) (0.2%) + SF (0.1%)                                                                  5     5     -     -                                      MCPB (Na salt) (0.1%)                                                                              1     0     +++   +++                                    MCPB (Na salt) (0.2%)                                                                              2     0     +++   +++                                    MCPB (Na salt) (0.1%) + SF (0.05%)                                                                 4.5   3     +     +                                      MCPB (Na salt) (0.1%) + SF (0.1%)                                                                  4.5   4     ±  ±                                   MCPB (Na salt) (0.2%) + SF (0.05%)                                                                 5     5     -     -                                      MCPB (Na salt) (0.2%) + SF (0.1%)                                                                  5     5     -     -                                      2,4,5-T (Na salt) (0.1%)                                                                           1     0     +++   +++                                    2,4,5-T (Na salt) (0.2%)                                                                           2     0     +++   +++                                    2,4,5-T (Na salt) (0.1%) + SF (0.05%)                                                              4.5   4     ±  ±                                   2,4,5-T (Na salt) (0.1%) + SF (0.1%)                                                               4.5   4     ±  ±                                   2,4,5-T (Na salt) (0.2%) + SF (0.05%)                                                              5     5     -     -                                      2,4,5-T (Na salt) (0.2%) + SF (0.1%)                                                               5     5     -     -                                      SL-501 (Na salt) (0.1%)                                                                            0.5   2     +++   ++                                     SL-501 (Na salt) (0.2%)                                                                            1     3     +++   ++                                     SL-501 (Na salt) (0.1%) + SF (0.05%)                                                               2.5   4     ++    -                                      SL-501 (Na salt) (0.1%) + SF (0.1%)                                                                3.5   5     ++    -                                      SL-501 (Na salt) (0.2%) + SF (0.05%)                                                               3.5   5     ±  -                                      SL-501 (Na salt) (0.2%) + SF (0.1%)                                                                4.5   5     ±  -                                      2,3,6-TBA (Na salt) (0.1%)                                                                         1     0     +++   +++                                    2,3,6-TBA (Na salt) (0.2%)                                                                         2     0     +++   +++                                    2,3,6-TBA (Na salt) (0.1%) + SF                                                                    4     3     +     +                                      (0.05%)                                                                       2,3,6-TBA (Na salt) (0.1%) + SF                                                                    4     3     ±  ±                                   (0.1%)                                                                        2,3,6-TBA (Na salt) (0.2%) + SF                                                                    5     5     -     -                                      (0.05%)                                                                       2,3,6-TBA (Na salt) (0.2%) + SF                                                                    5     5     -     -                                      (0.1%)                                                                        Banvel-D (Na salt) (0.1%)                                                                          1     0     +++   +++                                    Banvel-D (Na salt) (0.2%)                                                                          2     0     +++   +++                                    Banvel-D (Na salt) (0.1%) + SF                                                                     4     3     +     +                                      (0.05%)                                                                       Banvel-D (Na salt) (0.1%) + SF                                                                     4     4     -     -                                      (0.1%)                                                                        Banvel-D (Na salt) (0.2%) + SF                                                                     5     5     -     -                                      (0.05%)                                                                       Banvel-D (Na salt) (0.2%) + SF                                                                     5     5     -     -                                      (0.1%)                                                                        Amiben (Na salt) (0.1%)                                                                            1     0     +++   +++                                    Amiben (Na salt) (0.2%)                                                                            2     0     +++   +++                                    Amiben (Na salt) (0.1%) + SF (0.05%)                                                               4     3     +     +                                      Amiben (Na salt) (0.1%) + SF (0.1%)                                                                4     3     ±  ±                                   Amiben (Na salt) (0.2%) + SF (0.05%)                                                               5     5     -     -                                      Amiben (Na salt) (0.2%) + SF (0.1%)                                                                5     5     -     -                                      TPA (Na salt) (0.1%) 1     0     +++   +++                                    TPA (Na salt) (0.2%) 2     0     +++   +++                                    TPA (Na salt) (0.1%) + SF (0.05%)                                                                  4     3     +     +                                      TPA (Na salt) (0.1%) + SF (0.1%)                                                                   4     3     ±  ±                                   TPA (Na salt) (0.2%) + SF (0.05%)                                                                  5     5     -     -                                      TPA (Na salt) (0.2%) + SF (0.1%)                                                                   5     5     -     -                                      Dowco-233 (Na salt) (0.05%)                                                                        3     0     +     +++                                    Dowco-233 (Na salt) (0.1%)                                                                         4     0     +     +++                                    Dowco-233 (Na salt) (0.05%) + SF                                                                   5     2.5   ±  ±                                   (0.05%)                                                                       Dowco-233 (Na salt) (0.05%) + SF                                                                   5     3.5   ±  ±                                   (0.1%)                                                                        Dowco-233 (Na salt) (0.1%) + SF                                                                    5     5     -     -                                      (0.05%)                                                                       Dowco-233 (Na salt) (0.1%) + SF                                                                    5     5     -     -                                      (0.1%)                                                                        Glyphosate (0.05%)   1.5   1     +++   +++                                    (isopropylamine salt)                                                         Glyphosate (0.1%)    2.5   2     ++    ++                                     (isopropylamine salt)                                                         Glyphosate (0.05%) + SF (0.05%)                                                                    4     3.5   +     +                                      (isopropylamine salt)                                                         Glyphosate (0.05%) + SF (0.1%)                                                                     5     5     -     -                                      (isopropylamine salt)                                                         Glyphosate (0.1%) + SF (0.05%)                                                                     5     4.5   -     -                                      (isopropylamine salt)                                                         Glyphosate (0.1%) + SF (0.1%)                                                                      5     5     -     -                                      (isopropylamine salt)                                                         DPX-1108 (Na salt) (0.2%)                                                                          0     0     +++   ++*                                    DPX-1108 (Na salt) (0.4%)                                                                          0     0     +++   +*                                     DPX-1108 (Na salt) (0.2%) + SF                                                                     2     2.5   +     +                                      (0.05%)                                                                       DPX-1108 (Na salt) (0.2%) + SF                                                                     3     3.5   ±  ±                                   (0.1%)                                                                        DPX-1108 (Na salt) (0.4%) + SF                                                                     4.5   4.5   -     -                                      (0.05%)                                                                       DPX-1108 (Na salt) (0.4%) + SF                                                                     4.5   4.5   -     -                                      (0.1%)                                                                        NP-48 (0.15%)        1     2     +++   ++                                     NP-48 (0.3%)         1     3.5   +++   ++                                     NP-48 (0.15%) + SF (0.05%)                                                                         2.5   4     ++    -                                      NP-48 (0.15%) + SF (0.1%)                                                                          3     4.5   +     -                                      NP-48 (0.3%) + SF (0.05%)                                                                          3.5   5     ±  -                                      NP-48 (0.3%) + SF (0.1%)                                                                           4     5     ±  -                                      Linuron (0.1%)       3     2     +++   +++                                    Linuron (0.3%)       4     4     +++   +++                                    Linuron (0.1%) + SF (0.05%)                                                                        5     4     ++    +                                      Linuron (0.1%) + SF (0.1%)                                                                         5     5     +     +                                      Linuron (0.3%) + SF (0.05%)                                                                        5     5     -     ±                                   Linuron (0.3%) + SF (0.1%)                                                                         5     5     -     -                                      ATA (0.05%)          2     2     +++   +++                                    ATA (0.1%)           4     4     +++   +++                                    ATA (0.05%) + SF (0.05%)                                                                           4     4     -     -                                      ATA (0.05%) + SF (0.1%)                                                                            5     5     -     -                                      ATA (0.1%) + SF (0.05%)                                                                            5     5     -     -                                      ATA (0.1%) + SF (0.1%)                                                                             5     5     -     -                                      Choline hydrochloride (0.1%)                                                                       0     0     +++   +++                                    Choline hydrochloride (0.2%)                                                                       0     0     +++   +++                                    Choline hydrochloride (0.1%) + SF                                                                  3.5   3     ±  ±                                   (0.05%)                                                                       Choline hydrochloride (0.1%) + SF                                                                  4.5   4     -     -                                      (0.1%)                                                                        Choline hydrochloride (0.2%) + SF                                                                  5     5     -     -                                      (0.05%)                                                                       Choline hydrochloride (0.2%) + SF                                                                  5     5     -     -                                      (0.1%)                                                                        Diethylamine hydrochloride (0.1%)                                                                  0     0     +++   +++                                    Diethylamine hydrochloride (0.2%)                                                                  0     0     +++   +++                                    Diethylamine hydrochloride (0.1%) +                                                                3     2.5   +     +                                      SF (0.05%)                                                                    Diethylamine hydrochloride (0.1%) +                                                                4     3.5   -     -                                      SF (0.1%)                                                                     Diethylamine hydrochloride (0.2%) +                                                                5     4.5   -     -                                      SF (0.05%)                                                                    Diethylamine hydrochloride (0.2%) +                                                                5     5     -     -                                      SF (0.1%)                                                                     Untreated            0     0     +++   +++                                    ______________________________________                                         An anterisk (*) means growth retardation in height.                      

Table 8 shows that when the SF-1293 substances (A) or the compounds (B)is applied alone separately to Rumex obtusifolius and Zoysia japonica,there is obtained substantial damage of foliage of these weeds butlittle suppression of regrowth of these weeds from their undergroundroots, and that the combined use of the two components (A) and (B) canachieve complete suppression of such regrowth.

EXAMPLE 11

Aqueous solutions containing monosodium salt of SF-1293 substance andCMH, in admixture or separately, and 0.1% of octylphenylpolyoxyethanolas surfactant were applied at a rate of 150 l/10 ares to spontaneouslyoccurring perennial weeds at certain growth stage. Evaluation was madeby the same gradings as indicated in Example 10 both for damage toplants (assessed 21 days after treatment) and for suppression ofregrowth (assessed 4 months later).

The results are listed in Table 9 below.

                                      TABLE 9                                     __________________________________________________________________________                           Scale                                                                         21 Days                                                Test Compounds (Concentration in %)                                                                  Pc  Ap  Ro  Cy  Ic  Pr  An  Sc  Cp  Ch                 __________________________________________________________________________    SF-1293 (Na salt) (0.05%)                                                                            2   4   2.5 3   4   3   1   3   1   5                  SF-1293 (Na salt) (0.1%)                                                                             4   5   4   4   5   4.5 2   4   2   5                  SF-1293 (Na salt) (0.2%)                                                                             5   5   5   5   5   5   3   5   3   5                  SF-1293 (Na salt) (0.4%)                                                                             5   5   5   5   5   5   4.5 5   4.5 5                  CMH (0.3%)             0   1   0   0   0   0   0   0   0   1                  CMH (0.6%)             2   2   0   1   1   1   0   1   0   3                  SF-1293 (Na salt) (0.05%) + CMH (0.3%)                                                               3.5 5   4.5 4   4.5 4.5 3   4   2   5                  SF-1293 (Na salt) (0.05%) + CMH (0.6%)                                                               4.5 5   4.5 4   5   5   3   4   2   5                  SF-1293 (Na salt) (0.1%) + CMH (0.3%)                                                                5   5   5   4.5 5   5   4   5   4   5                  SF-1293 (Na salt) (0.1%) + CMH (0.6%)                                                                5   5   5   5   5   5   4   5   4   5                  SF-1293 (Na salt) (0.2%) + CMH (0.3%)                                                                5   5   5   5   5   5   5   5   5   5                  SF-1293 (Na salt) (0.2%) + CMH (0.6%)                                                                5   5   5   5   5   5   5   5   5   5                  Untreated              0   0   0   0   0   0   0   0   0   0                  __________________________________________________________________________                           Scale                                                                         4 Months                                               Test Compounds (Concentration in %)                                                                  Pc  Ap  Ro  Cy  Ic  Pr  An  Sc  Cp  Ch                 __________________________________________________________________________    SF-1293 (Na salt) (0.05%)                                                                            ++  +   ++  +++ +   ++  +   +++ +++ +++                SF-1293 (Na salt) (0.1%)                                                                             +   -   +   ++  ±                                                                              ±                                                                              -   ++  ++  ++                 SF-1293 (Na salt) (0.2%)                                                                             -   -   -   +   ±                                                                              ±                                                                              -   +   +   +                  SF-1293 (Na salt) (0.4%)                                                                             -   -   -   ±                                                                              -   -   -   +   +   +                  CMH (0.3%)             ++  ++  +++ +++ +++ ++ +                                                                              ++  ++  ++  ++                 CMH (0.6%)             +   +   +++ +++ +++ ++  ++  ++  ++  ++                 SF-1293 (Na salt) (0.05%) + CMH (0.3%)                                                               +   -   -   ++  ±                                                                              +   +   +   -   -                  SF-1293 (Na salt) (0.05%) + CMH (0.6%)                                                               -   -   -   ±                                                                              ±                                                                              ±                                                                              +   +   -   -                  SF-1293 (Na salt) (0.1%) + CMH (0.3%)                                                                -   -   -   -   -   -   -   -   -   -                  SF-1293 (Na salt) (0.1%) + CMH (0.6%)                                                                -   -   -   -   -   -   -   -   -   -                  SF-1293 (Na salt) (0.2%) + CMH (0.3%)                                                                -   -   -   -   -   -   -   -   -   -                  SF-1293 (Na salt) (0.2%) + CMH (0.6%)                                                                -   -   -   -   -   -   -   -   -   -                  Untreated              +++ +++ +++ +++ +++ +++ +++ +++ +++ +++                __________________________________________________________________________

The abbreviations of the test plants are assigned as follows:

Pc: Pleioblastus chino

Ap: Artemisia princeps

Ro: Rumex obtusifolius

Cy: Cayratia japonica

Ic: Imperata cyrindrica

Pr: Pueraria lobata

An: Athyrium nipinicium

Sc: Solanum carolinens

Cp: Cyperus rotundus

Ch: Calystegia hederacea

Table 9 clearly shows that the mixture of monosodium salt of SF-1293substance and CMH leads to remarkable improvement in suppression ofregrowth and exhibits a wider spectrum of weed control.

EXAMPLE 12

Formulations in the form of aqueous solutions similar to those used inExample 11 were applied at a rate of 150 l per 10 ares to plants growingin the areas of Chamaecyparis obtusa. 30 Days and 3 months after foliagetreatment, damage to plants was visually assessed on a scale of 0 to 5where 0 is no effect and 5 is complete kill as described in Example 6.

The results are set out in Table 10.

                                      TABLE 10                                    __________________________________________________________________________                          Scale                                                                         30 Days   3 Months                                      Test Compounds (Concentration in %)                                                                 Ch                                                                              Ct                                                                              Sa                                                                              Ms                                                                              Rc                                                                              Ch                                                                              Ct                                                                              Sa                                                                              Ms                                                                              Rc                                    __________________________________________________________________________    SF-1293 (Na salt) (0.125%)                                                                          0 5 3 3 4 0 3 2 2 3                                     SF-1293 (Na salt) (0.25%)                                                                           0 5 4 4 4.5                                                                             0 4 3 3 4                                     SF-1293 (Na salt) (0.5%)                                                                            0 5 5 5 5 0 5 4 4 5                                     CMH (0.25%)           0 0 0 0 0 0 0 0 0 0                                     CMH (0.5%)            0 1 1 1 1 0 0 1 0 1                                     CMH (1.0%)            0 3 2 2 2 0 1 2 1 2                                     SF-1293 (Na salt) (0.125%) + CMH (0.25%)                                                            0 5 4 4 4.5                                                                             0 5 4.5                                                                             4 4.5                                   SF-1293 (Na salt) (0.125%) + CMH (0.5%)                                                             0 5 4 4 4.5                                                                             0 5 5 4.5                                                                             5                                     SF-1293 (Na salt) (0.125%) + CMH (1.0%)                                                             0 5 4.5                                                                             4 4.5                                                                             0 5 5 5 5                                     SF-1293 (Na salt) (0.25%) + CMH (0.25%)                                                             0 5 5 4.5                                                                             5 0 5 5 4.5                                                                             5                                     SF-1293 (Na salt) (0.25%) + CMH (0.5%)                                                              0 5 5 5 5 0 5 5 5 5                                     SF-1293 (Na salt) (0.25%) + CMH (1.0%)                                                              0 5 5 5 5 0 5 5 5 5                                     SF-1293 (Na salt) (0.5%) + CMH (0.25%)                                                              0 5 5 5 5 0 5 5 5 5                                     SF-1293 (Na salt) (0.5%) + CMH (0.5%)                                                               0 5 5 5 5 0 5 5 5 5                                     SF-1293 (Na salt) (0.5%) + CMH (1.0%)                                                               0 5 5 5 5 0 5 5 5 5                                     Untreated             0 0 0 0 0 0 0 0 0 0                                     __________________________________________________________________________

The names of the test plants are assigned as follows:

Ch: Chamaecyparis obtusa

Ct: Castamea crenata

Sa: Sasa nipponica

Ms: Miscanthus sinensis

Rc: Rubus crataegifolius

Table 10 demonstrates that the mixture of monosidum salt of the SF-1293substance and CMH considerably enhances the regrowth-inhibitory effectof the sodium salt but is non-phytotoxic to useful woody plant,Chamaecyparis obtusa.

EXAMPLE 13

Formulations in the form of aqueous solutions similar to those used inExample 11 were applied at a rate of 100 l per 10 ares to spontaneouslyoccurring weeds, Echinochloa crusgali (abbreviated as Ec) and Digitariaadscendens (abbreviated as Dg) at intermediate growth stage. 14 Days andone month after foliage treatment, damage to plants was assessed.Besides, one month after treatment, degree of suppression of regrowthwas evaluated, by the same gradings as indicated in Example 11.

The test results are shown in Table 11.

                  TABLE 11                                                        ______________________________________                                                      Scale                                                                           14                                                            Test Compounds  Days     1 Month                                              (Concentration in %)                                                                          Ec    Dg     Ec      Dg                                       ______________________________________                                        SF-1293 (Na salt) (0.05%)                                                                     3     3      1   +++   1   +++                                SF-1293 (Na salt) (0.1%)                                                                      4     4      3   ++    3   ++                                 SF-1293 (Na salt) (0.2%)                                                                      5     5      4   ±  4   ±                               CMH (0.3%)      0     0      0   +++   0   +++                                CMH (0.6%)      1     1      0   +++   0   +++                                SF-1293 (Na salt) (0.5%) +                                                                    4     4      4   ±  4   ±                               CMH (0.3%)                                                                    SF-1293 (Na salt) (0.5%) +                                                                    4     4      4.5 ±  4.5 ±                               CMH (0.6%)                                                                    SF-1293 (Na salt) (0.1%) +                                                                    5     5      5   -     5   -                                  CMH (0.3%)                                                                    SF-1293 (Na salt) (0.1%) +                                                                    5     5      5   -     5   -                                  CMH (0.6%)                                                                    SF-1293 (Na salt) (0.2%) +                                                                    5     5      5   -     5   -                                  CMH (0.3%)                                                                    SF-1293 (Na salt) (0.2%) +                                                                    5     5      5   -     5   -                                  CMH (0.6%)                                                                    Untreated       0     0      0   +++   0   +++                                ______________________________________                                    

EXAMPLE 14

The area where various bushes and weeds were spontaneously growing wasdivided into plots of each 4 m², which was sprayed in autamn seasonevenly at a rate of 150 l per 10 ares with aqueous solutions containingsodium salt of SF-1293 substance and CMH, in admixture or separately,and containing further 0.1% of octylpheneylpolyoxyethanol as surfactant.7 Months after spraying, namely at the end of the next spring season,damage to plants was visually assessed on a scale of 0 to 5 where 0indicates no effect and 5 indicates complete kill as well as completesuppression of regrowth.

The results are shown in Table 12.

                  TABLE 12                                                        ______________________________________                                        Test Compounds Damage                                                         (Concentration in %)                                                                         Scale    Remarks                                               ______________________________________                                        SF-1293 (Na salt)                                                                            3.5      Hd 5, Fr 3, Rh 5, Pc 4.5                              (0.125%)                                                                      SF-1293 (Na salt)                                                                            4.5      Qu 5, Cb 4.5, Fr 4                                    (0.25%)                                                                       SF-1293 (Na salt)                                                                            5        Hd 5, Cb 5, Rh 5                                      (0.5%)                                                                        CMH (0.5%)     0.5-1    Cb 0.5, Rh 1.5-2, Hm 1.5                              CMH (1.0%)     1        Qu 3.5-4, Rh 3.5-4, Cb 0.5                                                    Slight damage to other                                                        plants                                                CMH (2.0%)     1-1.5    Ct 3.5-4, Cb 1, Rt 1                                                          Slight damage to other                                                        plants                                                SF-1293 (Na salt)                                                                            4.5      Pc 4.5-5 No substantial                               (0.125%) + CMH (0.5%)   regrowth of Sy and Hm                                 SF-1293 (Na salt)                                                                            4.5      No substantial regrowth                               (0.125%) + CMH (1.0%)   of Ln, Rh and Pc                                      SF-1293 (Na salt)                                                                            5        Great damage to Pc, Fr,                               (0.125%) + CMH (2.0%)   Hd, Am and others                                     SF-1293 (Na salt)                                                                            4.5      No substantial regrowth                               (0.25%) + CMH (0.5%)    of Cb, Rh, Pc and Fr                                  SF-1293 (Na salt)                                                                            5        No regrowth of Fr, Rh                                 (0.25%) + CMH (1.0%)    and Cb                                                SF-1293 (Na salt)                                                                            5        No regrowth                                           (0.25%) + CMH (2.0%)                                                          SF-1293 (Na salt)                                                                            5        No regrowth                                           (0.5%) + CMH (0.5%)                                                           SF-1293 (Na salt)                                                                            5        No regrowth                                           (0.5%) + CMH (1.0%)                                                           SF-1293 (Na salt)                                                                            5        No regrowth                                           (0.5%) + CMH (2.0%)                                                           Untreated plot 0        Hd 30 cm, Ln 20 cm,                                   (Height of plants)      Cb 50 cm Pc 75 cm,                                                            Rh 10-20 cm, Fr 25 cm                                 ______________________________________                                    

The names of the test plants are assigned as follows:

Hd: Hydrangea hirta

Fr: Fraxinus japonica

Rh: Rhododendron kaempferi

Pc: Pleioblastus chino

Qu: Quercus grossesenata

Cb: Clethra barbinervis

Hm: Hamamelis japonica

Ct: Castanea crenata

Rt: Rhus trichocarpa

Sy: Styrax japonica

Ln: Lyonia neziki

Am: Acer mono

EXAMPLE 15

In order to evaluate the herbicidal effect of the SF-1293 substancesagainst evergreen bushes, aqueous solutions similar to those used inExample 14 were applied at a rate of 100 l per 10 ares to Ternstroemiagymnanthera, Ligustrum japonicum and Rhaphiolepis umbellata (abbreviatedas Tr, Lg and Ru, respectively). 5 Months after foliage treatment,damage to plants was visually assessed by the same gradings as indicatedin Example 14.

The test results are tabulated in Table 13.

                  TABLE 13                                                        ______________________________________                                        Test Compounds + Scale                                                        (Concentration in %)                                                                           Lg         Tr    Ru                                          ______________________________________                                        SF-1293 Na salt (0.25%)                                                                        4.5        5     5                                           SF-1293 Na salt (0.5%)                                                                         5          5     5                                           CMH (0.5%)       2          2     2                                           CMH (1.0%)       3          2.5   2.5                                         CMH (2.0%)       3.5        3     3                                           SF-1293 Na salt (0.25%)                                                                        5          5     5                                           + CMH (0.5%)                                                                  SF-1293 Na salt (0.25%)                                                                        5          5     5                                           + CMH (1.0%)                                                                  SF-1293 Na salt (0.25%)                                                                        5          5     5                                           + CMH (2.0%)                                                                  SF-1293 Na salt (0.5%)                                                                         5          5     5                                           + CMH (0.5%)                                                                  SF-1293 Na salt (0.5%)                                                                         5          5     5                                           + CMH (1.0%)                                                                  SF-1293 Na salt (0.5%)                                                                         5          5     5                                           + CMH (2.0%)                                                                  Untreated        0          0     0                                           ______________________________________                                    

EXAMPLE 16

Aqueous solutions comprising sodium salt of SF-1293 substance as activeingredient and 0.1% of octylphenylpolyoxyethanol as surfactant wereapplied at a rate of 100 l/10 ares to Cyperus serotinus grown in aWagner porcelain pot of 1/5000 a in cross-section. The pot thus treatedwas allowed to stand outdoors for about 3 months. Then, the tubers wastaken from the underground soil in the pot and transferred into a deeppetri dish. The dish was placed in the greenhouse for emergence. 21 Dayslater, evaluation was made for prevention of emergence on a scale of 0to 5 where 0 is no effect and 5 is complete prevention of emergence.

The results are shown in Table 14.

                  TABLE 14                                                        ______________________________________                                        Test Compounds    Degree of Prevention of                                     (Concentration in %)                                                                            Emergence                                                   ______________________________________                                        SF-1293 (Na salt) (0.1%)                                                                        5                                                           SF-1293 (Na salt) (0.3%)                                                                        5                                                           Glyphosate (isopropylamine                                                                      5                                                           salt) (0.1%) (Control)                                                        Glyphosate (isopropylamine                                                                      5                                                           salt) (0.3%) (Control)                                                        Untreated         0                                                           ______________________________________                                    

What we claim is:
 1. A process for severely damaging or killing unwantedherbaceous and woody plants, which comprises applying to plantssusceptible thereto a herbicidally effective amount of SF-1293 substanceor an alkali metal, alkaline earth metal, copper, zinc, nickel,manganese, ammonium, substituted ammonium or acid-addition salt thereof,said SF-1293 substance or salt thereof being of the formula: ##STR4##wherein M¹ and M² are each hydrogen or a cation selected from the groupconsisting of sodium, potassium, lithium, copper, magnesium, calcium,zinc, nickel, maganese and ammonium which is unsubstituted orsubstituted by 1-4 lower alkyl, hydroxy lower alkyl, or lower alkenyl; Ais an inorganic or organic acid selected from the group consisting ofhydrochloric, sulfuric, hydrobromic, phosphoric, perchloric, nitric,acetic, propionic, citric, tartaric, monochloroacetic, trichloroaceticand trifluoroacetic acids; n is 0, 0.5 or 1; p is the inverse number ofthe valency of M¹ ; and q is the inverse number of the valency of M². 2.A process according to claim 1 in which the SF-1293 substance is a saltselected from the group consisting of the monosodium, disodium,monopotassium, dipotassium, mono(diethanolamine), mono(isopropylamine),mono(dimethylamine) and mono(n-butylamine) salts thereof.
 3. A processaccording to claim 1 for selectively controlling the growth of unwantedweeds and bushes in an area of useful woody plants, Chamaecyparisobtusa, an orchard or forestry land, wherein the SF-1293 substance orsalt thereof is applied in an amount sufficient to inhibit growth of theunwanted weeds and bushes but insufficient to substantially harm thedesired plants.